Antiseptic soap composition



United States NEISE TIC 50A! CQ I SIIIQN David J. Beaver, Richmond Heights, Roland S. Shumard',

Brentwood, and Ben! J. Sto feL. Elori santi Me. as.- signors to Monsanto Chemical Qompany, St. Louis, MQ'! p p ra iqn. o D laware No Drawi g. Application October 1 1952, Serialf N0. 312,667

6. Claims, (Qlr 2 52x401).

This ent on ates pm nd: us ful. comp s o of matter.

In accordance with this invention it has been found that halogenated tris-phenols of the general formula on 011 Xr-UCHz-UCHr CH3 xi Whe e X41. X2 and e ike or unlike, halhgm a m and their corresponding alkali metal salts. cjcpmprise a th h lx o h ghly spiul. compounds.

The new compounds have been found to have exceg. tiophl psritic. pr e es n smetip f simul ion a i in particular it has, been that the compounds. when. dm xed h t r en n. minor r o ti ns o de er nt om s ns hhi ti s ent h d ro ert s- Th ha ena ed i sh hols of? hi pventio i'ah heir:

l l o1-Ooi12OcHr- Cl OH; X2 CH5 and their corresponding mono-alkali metal salts where X2 is either a chlorine or a bromine atom. These trisphenols and their corresponding mono-alkali metal salts, e. g., the sodium, potassium and lithium salts, are readily prepared and are characterized by exceptional antiseptic properties when in admixture with a detergent and in cosmetic formulations.

As exemplary of the preferred halogenated tris-phenols of this invention are 4-chloro-a,a'-bis(Z-hydroxy 3 chloro-5-methylphenyl)- 2,6-xylenol 4-bromo-a,a'-bis(Z-hydroxy 3 chloro-5-methylphenyl)- 2,6-xylenol and their corresponding mono-alkali metal salts.

As exemplary of other tris-phenols of this invention which when admixed with a detergent form an efficient antiseptic detergent composition are:

atent 0 2,749,314 Patented June 5, 1956 -hromq-aaf-b s(z-hydtoxy brohio m y p y h 2,6:xylenol 4 chloroaa,a,bis.(Z-hydroxy 3 bromo-S-methylphenyD- 2,6-xylenol The pond ng alkali metal. sa ts. of hes halogenated phenols when incorporated in detergents. also produce satisfactory antiseptic detergent compositions As exemplary of the preparation of the newcompounds the following is illustrative:

EXAMPLE 1 wei h Qt o uen allowed. to s and. he solids be ng.

subsequently filte ed. of an dried. A y eld of appr ima ely 3 by, we htv o in he recry tall zed p uc is. a whit dlehli s o pos essing a melt ng. point f. 424.437 Upon. analy i the. pro uc is iound to. con ain 2.3 6% chlorine and is. el eved. o e. -ch rQ -a a'-b s(hhyd xy 3 chlor me hylphehyll- 2,6-xylenol,

The. white. soli s ium. salt d iva ive. here ob:- t i upon hea ing he. phenol wi h n equ ho e ma a oun f: odima hydroxid a queous me i m h wat r o he tea n; m d um. be n ptiy c bvvap r tetion.

E ploy ng he pr ess. oh Example I. but. r placing Q'ro-pcr sgl. with. neq mol r. amount of; 2..-br Q:

1 o xie d t, a. s idieved. o. b .-b :o..,o- 'I I (l-hy ro e3-chlorQ:5:me hy ph ny 2,6:xy epQl s o tain d...

The alkali me al sal s... p r icular y. t e mon -alkali metelsehsof thehalo enated dis-ph n ls O his. invention are conveniently prepared by heating in suitable proportions a halogenated tris-phenol of this invention with an aqueous solution of an alkali metal hydroxide, such as potassium hydroxide, sodium hydroxide or lithium hydroxide. However, the diand tri-alkali metal salts in many instances require more drastic conditions, as for example refluxing the tris-phenol with a mixture of alcohol and the alkali metal hydroxide in the necessary proportions.

As exemplary of this invention 4-chloro-a,a-bis(2- hydroxy-3-chloro-5-methylphenyl)-2,6-xylenol is compounded in a detergent composition and compared to detergent compositions which, respectively, contain analogous halogenated tris-phenols. The trisphenols listed below are, respectively, incorporated in an Ivory brand white high grade tallow soap to form 2% by weight compositions, that is a ratio of one part of halogenated trisphenol to 49 parts soap. Aliquots of each are added to a nutrient agar so as to give concentrations of 1.25 p. p. m., 5 p. p. m., and 10 p. p. m. of the halogenated tris-phenol in the nutrient agar. The agar in each case is then poured into a petri dish, allowed to harden and then is streaked with a 24 hour old culture of Staphylococcus aureus of standard resistance. The incubation in each case is made at 37 C. for 72 hours degree of growth is noted below:

and the Table I 10 1...) Halogenated Tris-Phenol p p m p m p UL 4-chloro-a,a-his (2-hydroxy-3-chloro-5- methylphenyD-Z fi-xylenol 4-chloro-a,a-bls (2-liydroxy-3-chloro-5- tert. butylphenyl)-Z,6-xylenol 0 4-chloro-a,a-bis (3-chloro-4-hydroxypheny1)-2,6-xyleu01 36+ Legend:

- No growth. 56+ Extremely light growth. Very light growth. Light to moderate growth.

+++ Normal heavy growth.

0 Not tested.

By replacing any one of the aforementioned halogenated tris-phenols of the aforedescribed detergent compositions with an equal weight of 4-bromo-a,a-bis(Z-hydroxy-S- chloro-S-methylphenyl)-2,6-xylenol and similarly evaluating excellent control of Staphylococcus aureus is obtained. Good control of Staphylococci is obtained by the usage of either 4-bromo-a,a-bis(2-hydroxy-3-bromo-5-methyl' phenyl)-2,6-xylenol, or 4-chloro-a,a'-bis(2-hydroxy-3- bromo-S-methylphenyl)-2,6-xylenol. Good control of Staphylococci is obtained also by the usage of the monosodium salts of 4chloro-a,a'-bis(2-hydroxy-3-chloro-5- methylphenyl)-2,6-xylenol and 4-bromo-a,a'-bis(2-hydroxy-3-chloro-5-methylphenyl)-2,6-xylenol.

Relatively small amounts of the halogenated tris-phenols of this invention or their alkali metal salts or mixtures of said phenols and said alkali metal salts in a detergent composition have been found to yield efficient antiseptic detergent compositions. Amounts as low as 0.54% by weight based upon the detergent of a halogenated trisphenol of this invention or its alkali metal salt or mixtures thereof have proved satisfactory in some instances. However, it is preferred to employ amounts in the order of 1-3% by weight. While larger amounts can be employed, as for example up to by weight, the upper limit is determined by practical considerations.

The term detergent includes soap and synthetic detergents, particularly the anionic detergents such as the substituted amides and the alkylated aryl sulfonates. The term detergent includes also mixtures of synthetic detergents and soap. The term soap or detergent soap" as used herein is employed in its popular or ordinary meaning, that is, those cleansing compositions prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.

The halogenated tris-phenols of this invention or the alkali metal salts thereof or mixtures thereof may be added to the detergent composition in any suitable manner during the crutching or milling or similar operation. The antiseptic agents of this invention may be first dissolved in a suitable solvent and then incorporated in the detergent if so desired. In general any method which results in the halogenated tris-phenols of this invention or their alkali metal salts thereof or mixtures of said phenols and said salts being uniformly incorporated in the final detergent composition is satisfactory.

While the invention has been described relative to several particular embodiments it is not so limited but that many variations and modifications which are obvious to those skilled in the art to which this invention appertains may be made without departing from the spirit or scope of the invention.

What is claimed is:

l. A halogenated tris-phenol of the formula CH; X: H:

where X1, X2 and X3 are halogen atoms selected from the group consisting of bromine and chlorine, and monosodium salts thereof.

2. 4 chloro-a,a'-bis( 2-hydroxy-3-chloro-5-methylphenyl)-2,6-xylenol.

3. 4 bromo a,a bis( 2 hydroxy-3-chloro-5-methylphenyl) -2,6-xylenol.

4. The mono-sodium salt of 4-chloro-a,a-bis(2-hydroxy-3-chloro-5-methylphenyl)-2,6-xylenol.

5. An antiseptic detergent composition comprising the combination of a detergent soap and l to 3% by weight based upon the detergent soap of 4-chloro-a,a'-bis(2-hydroxy-3-chloro-5-methylphenyl) -2,6-xylenol.

6. An antiseptic detergent composition comprising the combination of a detergent soap and l to 3% by weight based upon the detergent soap of 4-bromo-a,a-bis(2-hydroxy-3-chloro-5-methylphenyl)-2,6-xylenol.

References Cited in the file of this patent UNITED STATES PATENTS Gump July I8, 1944 Graige Mar. 13, ll

OTHER REFERENCES 

5. AN ANTISEPTIC DETERGENT COMPOSITION COMPRISING THE COMBINATION OF A DETERGENT SOAP AND 1 TO 3% BY WEIGHT BASED UPON THE DETERGENT SOAP OF 4-CHLORO-A,A''-BIS(2-HYDROXY-3-CHLORO-5-METHYLPHENYL)-2,6-XYLENOL. 